


What Lurks in the Dark

by CleverUsernameHere



Category: Supernatural
Genre: Anal Sex, Belly Bulging, Bottom Sam, Crack Fic ending, Double Penetration, Edging, M/M, Oral Sex, Other, Overstimulation, Tentacle Sex, Voyeurism
Language: English
Status: Completed
Published: 2020-03-17
Updated: 2020-03-17
Packaged: 2021-03-01 05:35:18
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,550
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23190035
Author URL: https://archiveofourown.org/users/CleverUsernameHere/pseuds/CleverUsernameHere
Summary: Dean finds himself in a very strange situation
Relationships: Dean Winchester/Sam Winchester, Dean Winchester/Tentacles, Sam Winchester/Tentacles
Comments: 7
Kudos: 152





	What Lurks in the Dark

**Author's Note:**

> This fills my ‘tentacles’ square for DeanAndSamBingo on my tumblr (@slut-for-Jared)

Dean searches the woods frantically, his feet carrying him as quickly as they can as he calls out for his brother. Dean doesn’t remember losing Sam in the woods. Hell, he doesn’t even remember going into the woods in the first place.

The sound of snapping twigs and leaves crinkling beneath his boots seems to echo around him. It’s so dark out- Dean can hardly see a mere few inches ahead of him. He keeps running, he keeps yelling for Sam, but Dean himself is now lost. He reaches for his gun, but finds it gone. Same with his knife. Dean curses- he must’ve been drunk or just stupid to go into the wilderness without any weapon. 

His shoulder connecting with the trunk of a tree is what it takes to make him stop running. Dean stumbles back, but he feels like he’s falling endlessly. 

“Hello!?” He turns his head in the direction Sam’s voice had called come from. Then he starts running towards it.

He comes to a clearing in the woods. The trees are high enough that there’s an open space. The leaves and branches aren’t as close together like the ones nearer to the ground, which allows bits of moonlight to crack through and shine on the ground. 

“Sammy!?” Dean cries, his eyes frantically searching the large, dimly lit area in front of him. Just a few yards away he spots what he hopes is Sam. But there’s something wrong, the shape is off. As Dean approaches with caution, he comes to realize that there’s something wrapped around his brother’s form, practically encasing him and pinning him to the ground.

The closer Dean gets, the more he can make out. Thick, black vines are wrapped around his brother’s body, maneuvering him in an odd way. They’re from the woods, they have to be. The length of them is spidering out, leading back into the trees in all different directions.

Dean feels like he’s been approaching forever, but no matter how much closer he thinks he’s getting, Sam seems to still be distant. He can hear Sam now, though. Little grunts and whimpers of pain leave his lips and Dean picks up the pace. He should’ve been there, he shouldn’t have left Sam’s side. 

He doesn’t even remember doing it, just like he didn’t remember them entering the woods, but he still chastises himself.

Dean starts to run again and that seems to actually work. He can make out Sam’s form clearly now and he nearly freezes in shock. Sam’s naked, his clothes nowhere in sight. He’s on his back, his hands held above his head and his legs hoisted in the air, his limbs wrapped in the large, black vines. They’re keeping him in place.

That’s when Dean realizes they aren’t vines. They look glossy and smooth to the touch. They look living, slithering and pulsing around Sam’s limbs every time he squirms. Dean told himself he had to be crazy, there was no way he was actually seeing tentacles wrapped around his brother’s naked body. 

When Sam starts to get louder, Dean realizes something else. There’s a thick tentacle wrapped around Sam’s arms and wrists, and one encircling each of his legs beneath the knee, holding his legs up and apart. But there’s a forth one that Dean had been too far away to notice. It’s thicker than the others, shiny and slick, and it’s moving between Sam’s spread legs. 

He’s close enough to get a good look and sure enough, his suspicions were confirmed. The tentacle between Sam’s legs is thrusting Itself in and out of Sam’s ass. Dean thought Sam’s previous cries were of anguish, but he quickly realizes they’re of pleasure when he sees Sam’s long, thick cock is hard and standing in attention.

“Sammy?” Dean doesn’t know what to do. Sam doesn’t look like he needs saving, hell, Dean wouldn’t even know how to. He ends up watching, even as he’s telling himself to fight the thing off. 

“Fuck,” Sam whimpers and Dean looks to his little brother. It’s like Sam doesn’t even notice Dean is standing a foot away. 

Sam’s pink lips are parted as he gasps and moans. His eyes flutter shut in bliss, even as he tries to keep them open. His whole body is jolting forward and then back from the power behind the tentacle’s thrusts.

Dean can’t fight his curiosity. His eyes cast down to below Sam’s exposed waist and Dean swears he can feel his own cock starting to fill out and harden. The thing is thrusting hard and fast between Sam’s spread legs, shoving itself so deep in his ass that his belly bulges out. Dean can’t stop himself from groaning at the sight.

The world around him seems to disappear. It’s like he’s suspended in space, just watching as the creature he only thought existed on the internet fucked his baby brother mindless. Sam’s legs are shaking in the monster’s hold as he cries out in pleasure. The thing seems to be going faster now, fucking into Sam ass at an incredible speed. 

Dean can actually hear how slick it is as it shoves in and out of Sam’s stretched hole. He hears the thick squelching sound of it going in and out, accompanied by the loud, whining moans that Sam released from his lips.

Suddenly, Dean feels something slithering up his ankle. He finally allowed his attention to fall away from his brother. He kicks his leg when he sees a tentacle move up his calf, but it squeezes harder and locks itself in place. “What the hell?” Dean mutters when he felt another one moving up his other leg.

He casts his eyes to Sam, which was a bad idea. His younger brother was flushed and panting, his eyes hazy with pleasure as he bucked his hips down. Sam was too busy enjoying himself. “Ah- ah- fuck-“ little gasping words were punched from Sam as the thing fucked itself as deep as it could go, stretching him out in a way Dean could never.

But Dean was too enthralled and sexually confused to be jealous. When Dean felt something moving around his waist, he was quickly refocusing himself on the tentacles on his body. In a flash another pair was wrapping around either of his arms, hoisting them above his head.

From what Dean could see, two smaller ones were working on his belt. Dean was speechless as his pants were being slowly dragged down his thighs. Then the smaller ones pulled his boxers down and Dean groaned when his cock sprang free.

Whatever this thing was, Dean couldn’t bring himself to fight it off. Another tentacle wrapped itself around Dean’s hardened cock and he grunted, but his own sounds were overpowered by the ones coming from Sam. Echoing pants and breathy moans were falling freely from Sam’s lips and Dean watched intensely. He knew Sam was close- he always knew. The sounds Sam made were a dead giveaway. 

Dean was suddenly forced to his knees as the tentacle around his cock started to stroke him. It slithered up and down his length in a way that had Dean moaning. 

He watched with lust filled eyes as the thing lifted one of Sam’s legs higher, like it was trying to give Dean the perfect view. Sam’s jaw dropped in a loud cry, but it was suddenly muffled by a gagging sound. Dean snapped his eyes from the tentacle in Sam’s ass to his face and- oh, god. 

Dean’s whole body shook in confused arousal when he saw that there was another tentacle now, forcing its way into Sam’s mouth. His brother was being fucked in both holes and Dean couldn’t help but groan as his cock twitched. 

Sam’s whole body was sheen with sweat, his cheeks were flushed, and now tears were dripping from his eyes as he sobbed out his pleasure around the thick, black tentacle. His cock was dripping precum, throbbing and slapping against his belly with each sharp movement of the tentacle in his ass.

Dean clenched his fists when the tentacle around his cock started to work overtime. Dean could tell that Sam was getting close, and evidently, the creature wanted him to be on that same edge. 

The tentacles fucking Sam’s mouth and ass seemed to be working in tandem, making Sam quiver in a way Dean could only dream of. He was gagging wetly around the thick one forcing its way down his throat, while the even thicker one in his ass forced him to shake with need.

Suddenly, the one in Sam’s mouth withdrew itself and Sam cried out. Dean watched, wide eyed and panting as Sam’s orgasm crashed over him. Thick spurts of white coated Sam’s belly as his cock twitched and pulsed. Dean was sure if the creature hadn’t been holding up his brother, Sam would’ve collapsed.

Dean’s jaw dropped when the thing kept going, fucking Sam through his orgasm and forcing him to feel the full extent of everything it had to offer. It had to be nailing his prostate- that much Dean knew. That was the only way to get Sam to scream like he was. It was too thick not to be rubbing against his sweet spot.

The tentacle around Dean’s cock kept jerking, forcing his pleasure to the surface. Dean was already so, so very close, but the creature was holding him right on edge. Dean tugged his arms, desperate to touch himself to grant his release, but the thick, black tentacles held him tight.

Sam tried to move, but he threw his head back as he sucked in ragged, choking gasps. He squirmed in its hold, but it kept going. The creature was relentless, stretching Sam open and fucking his ass hard. Dean wasn’t sure how much more his brother could take.

Sam yelped when the thing shoved itself deep and suddenly stopped. Dean’s jaw dropped when he saw Sam’s belly pushing out as he squirmed. Another dribble of cum forced its way from Sam’s softening cock and he gasped, tears dripping down his flushed cheeks from the intense stimulation while his whole body shuddered.

The black tentacle around Dean’s cock started to quicken its pace, pulling out all the stops to make him cum. Dean groaned and grunted as the thing worked him closer and closer to his impending orgasm. Dean dropped his head as he moaned, only for another tentacle to rest under his chin. It tilted his head back up, making sure he was watching Sam.

The thick, glossy, black tentacle was sliding out of Sam’s ass now. The other ones had gone, leaving Sam to lie limp on the ground. High pitched gasps that seemed so foreign fell from Sam’s lips as the thing withdrew. He clenched his eyes shut and his brow furrowed. 

Then thing pulled out fully with a slick pop and that’s what finally pushed Dean over the edge. The shiny, black tentacle was thicker than he thought. It was bigger than Dean’s bicep and knowing that it had been in his brother’s ass, stretching him out beyond belief and forcing his pleasure was too much to handle. Dean came with a loud groan, his whole body quaking as the thing worked his cock. He watched Sam, who finally opened his eyes. He was looking right at Dean. 

Sam’s hand was moving down and Dean followed it. Sam’s fingers stroked through the mess of cum on his belly and Dean bit his lip as his own cock spurted his release. Sam brought his cum coated fingers to his lips, his eyes locked with Dean’s the entire time. He didn’t even look away when he pushed his fingers into his mouth.

“Oh fuck-“ Dean grunted, his eyes clenching shut in renewed arousal at the sight. His cock gave another twitch and the tentacle finally released it’s hold. Then the ones around his limbs released him, just like they had with Sam. Dean fell to the ground with a huff.

Then he snapped his eyes open. Yellow tinted light surrounded him and Dean sat up immediately. He looked around and quickly realized he was back in the motel room. He was sitting upright in a wooden chair at a small, round table. 

“Dude, are you okay?” Dean whipped his head to the side at the sound of his brother’s voice. Sure enough, Sam was sitting a few feet away from him, an expression of amusement and confusion crossing his face. 

“I-“ Dean’s mouth felt so dry as he swallowed. Dean didn’t know what to say. It was like his mind was blank. 

“Must’ve been one serious dream.” Sam commented with a huffing laughter and Dean swallowed.

“Dream?” Dean questioned slowly, his brows furrowing at his brother. Sam just rolled his eyes and huffed out another laugh.

“Yeah, Dean, you fell asleep in the middle of us researching.” Sam reminded with a hint of annoyance behind his confusion. Dean’s eyes locked with Sam’s and he nodded, muttering an apology, but he hardly had listened after the word ‘dream’. “You kept makin’ all these weird noises…” Sam grumbled.

It was like the images from his dream replayed over again and again. Sam, in the middle of the woods, getting his ass fucked open by a tentacle creature. Then Sam gets fucked in both holes by the thing. Then Sam cumming all over himself, and then finally sucking his own cum off of his fingers. Dean felt his body heat up at just the thought. He was ready to stand from the table- he needed to get away from his brother just for a moment. Dean needed to clear his head from the dream that had been disturbingly vivid. He started to stand, but froze.

Dean looked to his lap and internally cursed- he’d cum in his pants like a damn teenager. He shifted in his seat and clenched his teeth. His jeans were sticky with his own seed and his cock was still sensitive after cumming. There was actually a dark, wet patch on the front of his pants. Dean couldn’t remember the last time he had cum that much- or the last time he had cum in his sleep.

“You okay?” Sam questioned again and Dean swallowed thickly, wiping his sweaty palms against his jean clad thighs. Sam would never let him live this down, so he kept quiet and nodded. “So can I have my laptop back then?” Dean furrowed his brows and Sam rolled his eyes. His brother reached forward and snatched his laptop from in front of Dean. 

Dean took that opportunity to scramble from the chair and into the bathroom. He locked the door behind him and exhaled a sigh of relief. He just needed a shower and then he could get his head back in the game.

Sam scoffed at Dean’s antics as he opened his laptop and re-powered it up. He yanked out Dean’s earbuds from the jack as he logged back in. “Oh, come on!” Sam exclaimed when he saw the page his brother had been on. He muted it quickly and closed out of the tabs. “How many times do I have to tell you to not watch your creepy anime porn on my laptop, Dean!?”

**Author's Note:**

> I’ve never written anything like this before, so feedback would be super awesome :)
> 
> It takes less than a second to leave a kudos, even if you’re a guest and they’re much appreciated, same with comments <3


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